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James Van Der Beek on Lessons From 'Apartment 23,' Stand-Up and Dawson Comparisons

"Friends With Better Lives" Trae Patton/CBS

The "Friends With Better Lives" star chats with THR about his shift to comedy, what would have happened on a third season of the ABC comedy and wanting to work with Will Ferrell.

James Van Der Beek has gone from playing a hopeless romantic on Dawson's Creek to reinventing himself as a comedic actor by mocking his early days on The WB network in ABC's Don't Trust the B---- in Apartment 23. Now the Cruel Intentions and Varsity Blues alum will step into the role of Will Stokes, a sad sack who must reinvent himself after his marriage crumbles on CBS' freshman comedy Friends With Better Lives.

From Friends alum Dana Klein, the ensemble comedy revolves around a group of 30-something friends who each think the other has it better. The comedy marks Van Der Beek's first scripted half-hour and first multicamera series and brings the theater alum back to working in front of a live audience.

The Hollywood Reporter caught up with Van Der Beek to discuss his second coming as a comedic actor, what he learned from two seasons of mocking himself on Apartment 23, where he played a heightened version of himself, as well as what his next comedic goals are (hint: more Funny or Die videos and an Apartment 23 reunion).

I didn't, actually. I thought I wanted to do a really dark drama or something gritty on cable, and then Dana and Aaron Kaplan approached me to do this. Dana presented me with the idea of playing this character -- who thought he had the rest of his married life figured out, is thrust into the single world and having to discover who he is. I thought it was a great journey and it was a great schedule. (Laughs.) I get to put my kids to bed four to five nights a week. It's also live audience, and having started in the theater, I missed that live audience. There's something about the live audience that keeps the comedy honest. It's old-school and it's what us weird theater freaks have been doing since the beginning of time. And it was James Burrows directing -- that was the clincher.

How have you adjusted from playing a heightened version of yourself to a character again?

It is fun to play someone who is a little bit less out there. It's been interesting to figure out what works comedically because the fake version of me -- as soon as I started going down that road, I went to the Upright Citizens Brigade Theatre and I hosted an awards show and had to find out what people found funny in this exaggerated version of me. For this, we had to create it with the writers. It's been a journey, and Will has his peccadilloes for sure.

Do you miss having fun at your own expense?

I do. I miss the crazy stuff that I got to do on Apartment 23. It was a really fun character to play because he was completely without shame. It's fun to mock the business, and it's fun to keep your own ego in check, too. You feel very safe when you're constantly destroying all those little things you keep precious as an actor. It's a very liberating feeling. I'll probably find a way to do more of it here and there. I've talked to [Apartment 23 co-star] Ray Ford about doing something for Funny or Die, which is in the planning stages.

What kind of comedy lessons did you learn from doing Apartment 23? How did that prepare you for what you're doing now?

I learned a lot about grounding comedy and balance as well as how to get laughs without the audience feeling sorry for you. We wanted things to blow up in this guy's face, but the counterbalance to that was he had to be really good at what he does instantly, in a savant-ish kind of way, because otherwise, it's sad. We could have him be completely clueless and totally narcissistic, but then also very sincere in everything that he says, so it was about finding that formula that worked. I did go back to that in figuring out who Will is and finding that balance. Will is incredibly particular, clueless and cynical about many things, but there are other sides where he's just so stupidly romantic that you think nobody like this exists.

Had Apartment 23 gone to a third season, what do you think Fake James would be up to?

Well, [showrunner] Nahnatchka Khan and I were always knocking things back and forth. There was a musical version of the cop drama he wrote at the end of season one, Fingered: The Musical, and taking that to Broadway. (Laughs.) There seemed to be an endless well of ridiculous, stupid things that he could get into.

Is there anything you didn't get to do on that show that you wish you had?

There was talk of going to Monte Carlo to shoot the Woody Allen movie Monte Carlo Monte Carla. Had there been a back-nine, our producer Jeff Morton had been working toward us going there. (Laughs.)

There has been no shortage of Friends-type relationship comedies. How does Friends With Better Lives separate itself from the rest?

It's all about chemistry and good, honest writing and a scenario with good enough points of view for people to be honest about funny stuff that happens in real life and a big enough sandbox to really be able to go there. I hope the chemistry that we have on-set and with each other comes across. What I look for in a sitcom is if I want to hang out with these people; do I want them to be my friends. You don't want to go too far in the name of comedy that it makes people not want to spend time with these guys.

In the pilot, Will is very much a hopeless romantic -- which is very reminiscent of Dawson Leery, the eternal dreamer. Do you think the two characters have anything in common?

That's interesting; I never thought about that. Dawson's Creek happened so long ago that I stopped referencing it. For a while right afterward I was very determined to not do anything that had anything to do with that character. Then I just stopped caring. It's the same actor years later so it makes sense that certain characteristics would pop up here and there, but there's a real peculiarity to Will to offset this romantic nature that he has. He's also clueless, so … (laughs).

What have you learned from the multicamera format?

Diction counts for a lot. (Laughs.) When I started in theater, my diction was not always the best. In drama, you want the audience to be asking questions about what's going on, what a character is really feeling. In comedy, if you're asking questions, you're not laughing. But surprise is where the laugh comes. So you have to keep the audience going along without raising too many questions and then surprise them. You have to resist the temptation to always go for the laugh and just revel in it. You can't be a pig about it and you can't be too much of a ham.

You've done UCB, Funny or Die, mocked yourself for laughs and now this. What's the next step in your comedic career? Have you ever wanted to do stand-up?

If I had the balls to do stand-up, I would probably start at a free club somewhere and just fall on my face. You have to fall on your face so many times in order for that to work. I'd love to try in some features. The studio comedies right now seem to be working. What I'd really love to do is work with Will Ferrell, Ben Stiller, Vince Vaughn and Owen Wilson -- those guys who just crush it -- and learn and watch how they transition those skills onto film.

Are those your comedic role models? Who inspires your approach to comedy?

Ted Danson was probably the gold standard for sitcom work. Kelsey Grammer and Tim Allen are fantastic at multicam. I've been watching a lot of episodes of Cheers, Frasier and The Golden Girls; those are the black belts. The writing is so good, too.

Is there a current comedy that you make a point to watch?

The Big Bang Theory. Those guys are crushing it.

Would you want to guest-star?

I'd be down, sure. I wonder if it'd be weird. Cross-promotion? Why not! In terms of appointment viewing on my DVR, I record Louie; Louis C.K. is probably my favorite.

What do you think Fake James would say about Friends With Better Lives' Will if the two were to cross paths in some crazy alternate universe?